title: Biomass-derived chemicals: synthesis of biodegradable surfactant ether molecules from hydroxymethylfurfural.
abstract: A new class of biodegradable anionic surfactants with structures based on 5-alkoxymethylfuroate was prepared starting from 5-hydroxymethylfurfural (HMF), through a one-pot-two-steps process which involves the selective etherification of HMF with fatty alcohols using heterogeneous solid acid, followed by a highly selective oxidation of the formyl group with a gold catalyst. The etherification step was optimized using aluminosilicates as acid catalysts with different pore topologies (H-Beta, HY, Mordenite, ZSM-5, ITQ-2, and MCM-41), different active sites (Bronsted or Lewis) and different adsorption properties. It was shown that highly hydrophobic defect-free H-Beta zeolites with Si/Al ratios higher than 25 are excellent acid catalysts to perform the selective etherification of HMF with fatty alcohols, avoiding the competitive self-etherification of HMF. Moreover, the 5-alkoxymethylfurfural derivatives obtained can be selectively oxidized to the corresponding furoic salts in excellent yield using Au/CeO2 as catalyst and air as oxidant, at moderated temperatures. Both H-Beta zeolite and Au/CeO2 could be reused several times without loss of activity.
authors.affiliation: Instituto de Tecnología Química (UPV-CSIC), Universitat Politècnica de València, Avda dels Tarongers s/n, 46022, Valencia (Spain), Fax: (+34) 963877809.
authors.forename: Karen S
authors.initials: KS
authors.lastname: Arias
authors.forename: Maria J
authors.initials: MJ
authors.lastname: Climent
authors.forename: Avelino
authors.initials: A
authors.lastname: Corma
authors.forename: Sara
authors.initials: S
authors.lastname: Iborra
mesh_terms: D000538:Aluminum Silicates / Q000737:chemistry*; D018533:Biomass; D002384:Catalysis; D002563:Cerium / Q000737:chemistry; D004987:Ethers / Q000737:chemistry*; D005662:Furaldehyde / Q000031:analogs & derivatives* / Q000737:chemistry; D006046:Gold / Q000737:chemistry; D012822:Silicon Dioxide / Q000737:chemistry*; D013501:Surface-Active Agents / Q000737:chemistry*
chemical_list: D000538:Aluminum Silicates; D004987:Ethers; C509968:MCM-41; D013501:Surface-Active Agents; D002563:Cerium; C030583:ceric oxide; C008046:5-hydroxymethylfurfural; D006046:Gold; D012822:Silicon Dioxide; D005662:Furaldehyde
keywords: 5-hydroxymethylfurfural; biomass; heterogeneous catalysis; surfactants; zeolites